Synthesis and conformational behavior of pseudopeptides containing delta-azaproline. A cis conformational preference for Xaa(1)-delta-azaPro bond

Abstract : delta-Azaproline, a new bis-nitrogen proline surrogate has been used in order to control the conformation of an AA-Psi Pro bond. Conformational analysis of Xaa(1)-delta-azaPro-Xaa(3) performed by NMR, IR experiments, and molecular modeling revealed a preference for a trans conformation of the Xaa(1)-delta-azaPro bond when delta-azaPro is protected by a Boc group. The removal of the Boc protection leads to the establishment of a C-10 pseudocycle via a hydrogen bond network favoring the cis conformation of the Xaa(1)-delta-azaPro bond.
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Tetrahedron, Elsevier, 2014, 70 (2), pp.363-370. 〈10.1016/j.tet.2013.11.049〉
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https://hal.univ-lorraine.fr/hal-01498198
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Soumis le : mercredi 29 mars 2017 - 16:52:15
Dernière modification le : jeudi 11 janvier 2018 - 06:27:33

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Emelyne Humbert-Voss, Axelle Arrault, Brigitte Jamart-Grégoire. Synthesis and conformational behavior of pseudopeptides containing delta-azaproline. A cis conformational preference for Xaa(1)-delta-azaPro bond. Tetrahedron, Elsevier, 2014, 70 (2), pp.363-370. 〈10.1016/j.tet.2013.11.049〉. 〈hal-01498198〉

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